NO315465B1 - Fremgangsmåte for fremstilling av arylamider av heteroaromatiske karboksylsyrer - Google Patents
Fremgangsmåte for fremstilling av arylamider av heteroaromatiske karboksylsyrer Download PDFInfo
- Publication number
- NO315465B1 NO315465B1 NO19971315A NO971315A NO315465B1 NO 315465 B1 NO315465 B1 NO 315465B1 NO 19971315 A NO19971315 A NO 19971315A NO 971315 A NO971315 A NO 971315A NO 315465 B1 NO315465 B1 NO 315465B1
- Authority
- NO
- Norway
- Prior art keywords
- nitrogen
- ring
- optionally substituted
- formula
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- -1 heteroaromatic carboxylic acids Chemical class 0.000 title claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 23
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 150000002366 halogen compounds Chemical class 0.000 claims abstract description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 5
- 150000003624 transition metals Chemical class 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 150000001408 amides Chemical class 0.000 claims description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 125000000217 alkyl group Chemical group 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 101150065749 Churc1 gene Proteins 0.000 abstract 1
- 102100038239 Protein Churchill Human genes 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000008096 xylene Substances 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 11
- 150000003335 secondary amines Chemical class 0.000 description 11
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 8
- UXNQGJXYCPLETH-UHFFFAOYSA-N C1(=CC=CC=C1)P(C=1[C-](C=CC1)C(C)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound C1(=CC=CC=C1)P(C=1[C-](C=CC1)C(C)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.[CH-]1C=CC=C1.[Fe+2] UXNQGJXYCPLETH-UHFFFAOYSA-N 0.000 description 7
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LFVNBAYLMRRFQM-UHFFFAOYSA-N 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=C(Cl)C=CC=2)=C1 LFVNBAYLMRRFQM-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- OHWWNYSXSGMTSB-UHFFFAOYSA-N cyclopenta-1,3-diene;ditert-butyl-[1-(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)ethyl]phosphane;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.CC(C)(C)P(C(C)(C)C)C(C)[C-]1C=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 OHWWNYSXSGMTSB-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 102220007331 rs111033633 Human genes 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WVSBQYMJNMJHIM-UHFFFAOYSA-N (benzene)chromium tricarbonyl Chemical group [Cr].[O+]#[C-].[O+]#[C-].[O+]#[C-].C1=CC=CC=C1 WVSBQYMJNMJHIM-UHFFFAOYSA-N 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- BINQYVWLAWZYPX-UHFFFAOYSA-N 1,3,5-triazine-2-carboxylic acid Chemical class OC(=O)C1=NC=NC=N1 BINQYVWLAWZYPX-UHFFFAOYSA-N 0.000 description 1
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- MFDBYHAXXAGPNF-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=CC=CC=2)=C1 MFDBYHAXXAGPNF-UHFFFAOYSA-N 0.000 description 1
- ZZXWXGVXVLZNFK-UHFFFAOYSA-N 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyrazine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=C(Cl)C=NC=2)=C1 ZZXWXGVXVLZNFK-UHFFFAOYSA-N 0.000 description 1
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
- JHFQIWDOKUTRBA-UHFFFAOYSA-N 3-chloro-2-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC=CN=2)Cl)=C1 JHFQIWDOKUTRBA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XRGZZAZQHRUQLU-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C(=NC(=CC1)OC1=CC(=CC=C1)C(F)(F)F)C(=O)N Chemical compound FC1=CC=C(C=C1)C=1C(=NC(=CC1)OC1=CC(=CC=C1)C(F)(F)F)C(=O)N XRGZZAZQHRUQLU-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
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- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/82—Metals of the platinum group
- B01J2523/824—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/84—Metals of the iron group
- B01J2523/842—Iron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH73596 | 1996-03-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO971315D0 NO971315D0 (no) | 1997-03-20 |
| NO971315L NO971315L (no) | 1997-09-22 |
| NO315465B1 true NO315465B1 (no) | 2003-09-08 |
Family
ID=4193980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19971315A NO315465B1 (no) | 1996-03-21 | 1997-03-20 | Fremgangsmåte for fremstilling av arylamider av heteroaromatiske karboksylsyrer |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US5922870A (de) |
| EP (1) | EP0798296B1 (de) |
| JP (1) | JP4138905B2 (de) |
| KR (1) | KR100508740B1 (de) |
| CN (1) | CN1071320C (de) |
| AT (1) | ATE256113T1 (de) |
| CA (2) | CA2199786C (de) |
| CZ (1) | CZ289783B6 (de) |
| DE (1) | DE59711086D1 (de) |
| DK (1) | DK0798296T3 (de) |
| ES (1) | ES2212005T3 (de) |
| HU (1) | HU220171B (de) |
| NO (1) | NO315465B1 (de) |
| PL (1) | PL191593B1 (de) |
| PT (1) | PT798296E (de) |
| SK (1) | SK284024B6 (de) |
| TW (1) | TW472044B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE256113T1 (de) * | 1996-03-21 | 2003-12-15 | Lonza Ag | Verfahren zur herstellung von arylamiden heteroaromatischer carbonsäuren |
| US7912205B2 (en) * | 2004-12-17 | 2011-03-22 | Aspect Software, Inc. | Contact center business modeler |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128554A (en) * | 1974-05-10 | 1978-12-05 | University Of Delaware | Process for the preparation of carboxylic acid amides from organic halides |
| NZ188244A (en) * | 1977-09-13 | 1981-04-24 | Ici Australia Ltd | 2-substituted pyrimidines compositions growth regulating processes |
| US4254125A (en) * | 1980-04-07 | 1981-03-03 | The Dow Chemical Company | 2-Chloro-3-phenoxypyrazines and 2-chloro-6-phenoxypyrazines possessing antiviral activity |
| IL64220A (en) * | 1980-11-21 | 1985-06-30 | May & Baker Ltd | Nicotinamide derivatives,their preparation and their use as herbicides |
| US5159113A (en) * | 1984-12-19 | 1992-10-27 | The B. F. Goodrich Company | Process for the palladium-catalyzed amidation of vinyl chloride |
| CH664754A5 (en) * | 1985-06-25 | 1988-03-31 | Lonza Ag | 5,6-di:chloro-nicotinic acid prodn. - by reacting 6-hydroxy-nicotinic acid with acid chloride, reacting prod. with chlorine, then with acid chloride and hydrolysing prod |
| JPS62138472A (ja) * | 1985-12-11 | 1987-06-22 | Mitsui Toatsu Chem Inc | ２，６−ビス（４−アミノフエノキシ）ピリジンおよびその製造方法 |
| JPS62142161A (ja) * | 1985-12-16 | 1987-06-25 | Mitsui Toatsu Chem Inc | ２，６−ビス（３−カルボキシフエノキシ）ピリジンおよびその製造方法 |
| JPH0819009B2 (ja) * | 1987-03-12 | 1996-02-28 | 日本農薬株式会社 | カルボン酸アミド類の製造法 |
| IL91083A (en) * | 1988-07-25 | 1993-04-04 | Ciba Geigy | Cyclohexanedione derivatives, their preparation and their use as herbicides |
| CA2008878C (en) * | 1989-02-28 | 2003-01-21 | Michelangelo Scalone | Process for preparing pyridine-2-carboxamides |
| DE4020055A1 (de) * | 1990-01-18 | 1991-07-25 | Bayer Ag | Verfahren zur herstellung von substituierten 2-chlor-pyridinen |
| GB9005965D0 (en) * | 1990-03-16 | 1990-05-09 | Shell Int Research | Herbicidal carboxamide derivatives |
| EP0461401A1 (de) * | 1990-06-15 | 1991-12-18 | American Cyanamid Company | Verfahren zur Herstellung von 2,3-Pyridindicarbonsäure-dialkylestern aus Dialkyldichloromaleinsäureestern |
| GB9025828D0 (en) * | 1990-11-28 | 1991-01-09 | Shell Int Research | Herbicidal carboxamide derivatives |
| DE4207604A1 (de) * | 1991-03-13 | 1992-09-17 | Ciba Geigy Ag | Schaedlingsbekaempfungsmittel |
| US5166352A (en) * | 1991-09-12 | 1992-11-24 | Dowelanco | Pyridinecarboxylic acid chlorides from (trichloromethyl)pyridines |
| US5288866A (en) * | 1991-12-20 | 1994-02-22 | American Cyanamid Company | 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds useful for the preparation of 5- (substituted methyl)-2,3-pyridinedicarboxylic acids |
| EP0564406B1 (de) * | 1992-04-02 | 1999-05-06 | Novartis AG | Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
| DE59410267D1 (de) * | 1993-02-26 | 2003-05-15 | Syngenta Participations Ag | Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
| EP0700391B1 (de) * | 1993-05-27 | 1998-10-21 | Shell Internationale Researchmaatschappij B.V. | Herbizide verbindungen |
| CA2539969C (en) * | 1993-06-01 | 2009-07-07 | Lonza Ltd. | Process for the preparation of carboxylic acids of nitrogen-containing aromatic heterocyclic compounds |
| DE59408655D1 (de) * | 1993-10-01 | 1999-09-30 | Novartis Ag | Mit Fluoralkyl substituierte Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
| DE4410480A1 (de) * | 1994-03-25 | 1995-09-28 | Hoechst Ag | Sulfonamidocarbonylpyridin-2-carbonsäureesteramide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US5464106A (en) * | 1994-07-06 | 1995-11-07 | Plastipak Packaging, Inc. | Multi-layer containers |
| ATE256113T1 (de) * | 1996-03-21 | 2003-12-15 | Lonza Ag | Verfahren zur herstellung von arylamiden heteroaromatischer carbonsäuren |
| US5900484A (en) * | 1996-09-18 | 1999-05-04 | Lonza Ag | Process for the preparation of arylamides of heteroaromatic carboxylic acids |
| DK0806415T3 (da) * | 1996-05-09 | 2000-06-05 | Lonza Ag | Fremgangsmåde til fremstilling af arylamider af heteroaromatiske carboxylsyrer |
-
1997
- 1997-03-10 AT AT97103981T patent/ATE256113T1/de not_active IP Right Cessation
- 1997-03-10 EP EP97103981A patent/EP0798296B1/de not_active Expired - Lifetime
- 1997-03-10 DK DK97103981T patent/DK0798296T3/da active
- 1997-03-10 DE DE59711086T patent/DE59711086D1/de not_active Expired - Fee Related
- 1997-03-10 PT PT97103981T patent/PT798296E/pt unknown
- 1997-03-10 ES ES97103981T patent/ES2212005T3/es not_active Expired - Lifetime
- 1997-03-12 CA CA002199786A patent/CA2199786C/en not_active Expired - Fee Related
- 1997-03-12 CA CA002504399A patent/CA2504399C/en not_active Expired - Fee Related
- 1997-03-12 SK SK322-97A patent/SK284024B6/sk not_active IP Right Cessation
- 1997-03-13 US US08/816,692 patent/US5922870A/en not_active Expired - Fee Related
- 1997-03-14 JP JP06135897A patent/JP4138905B2/ja not_active Expired - Fee Related
- 1997-03-15 TW TW086103236A patent/TW472044B/zh not_active IP Right Cessation
- 1997-03-18 KR KR1019970009205A patent/KR100508740B1/ko not_active IP Right Cessation
- 1997-03-20 NO NO19971315A patent/NO315465B1/no not_active IP Right Cessation
- 1997-03-20 HU HU9700616A patent/HU220171B/hu not_active IP Right Cessation
- 1997-03-20 CZ CZ1997852A patent/CZ289783B6/cs not_active IP Right Cessation
- 1997-03-21 CN CN97104882A patent/CN1071320C/zh not_active Expired - Lifetime
- 1997-03-21 PL PL319086A patent/PL191593B1/pl not_active IP Right Cessation
-
1999
- 1999-03-30 US US09/280,975 patent/US6175011B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SK284024B6 (sk) | 2004-08-03 |
| DK0798296T3 (da) | 2004-04-05 |
| CN1169990A (zh) | 1998-01-14 |
| PL191593B1 (pl) | 2006-06-30 |
| PL319086A1 (en) | 1997-09-29 |
| HU220171B (hu) | 2001-11-28 |
| TW472044B (en) | 2002-01-11 |
| HUP9700616A3 (en) | 1999-05-28 |
| ES2212005T3 (es) | 2004-07-16 |
| CZ289783B6 (cs) | 2002-04-17 |
| CA2504399C (en) | 2009-09-15 |
| NO971315L (no) | 1997-09-22 |
| US5922870A (en) | 1999-07-13 |
| EP0798296A3 (de) | 1999-01-13 |
| KR970065518A (ko) | 1997-10-13 |
| SK32297A3 (en) | 1998-01-14 |
| CZ85297A3 (en) | 1997-10-15 |
| JP4138905B2 (ja) | 2008-08-27 |
| CA2199786A1 (en) | 1997-09-21 |
| HUP9700616A2 (en) | 1997-12-29 |
| CN1071320C (zh) | 2001-09-19 |
| US6175011B1 (en) | 2001-01-16 |
| CA2504399A1 (en) | 1997-09-21 |
| JPH107655A (ja) | 1998-01-13 |
| DE59711086D1 (de) | 2004-01-22 |
| HU9700616D0 (en) | 1997-05-28 |
| EP0798296A2 (de) | 1997-10-01 |
| CA2199786C (en) | 2005-08-09 |
| KR100508740B1 (ko) | 2006-03-23 |
| NO971315D0 (no) | 1997-03-20 |
| EP0798296B1 (de) | 2003-12-10 |
| ATE256113T1 (de) | 2003-12-15 |
| PT798296E (pt) | 2004-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |